HU191510B - Insecticide and acaricide compositions containing fluoro-phenoxy-benzyl-esters and process for preparing the active substances - Google Patents
Insecticide and acaricide compositions containing fluoro-phenoxy-benzyl-esters and process for preparing the active substances Download PDFInfo
- Publication number
- HU191510B HU191510B HU409782A HU409782A HU191510B HU 191510 B HU191510 B HU 191510B HU 409782 A HU409782 A HU 409782A HU 409782 A HU409782 A HU 409782A HU 191510 B HU191510 B HU 191510B
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- formula
- cis
- cyano
- active ingredient
- phenoxy
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- 239000000203 mixture Substances 0.000 title claims description 30
- 230000000895 acaricidal effect Effects 0.000 title claims description 14
- 239000013543 active substance Substances 0.000 title description 3
- 239000000642 acaricide Substances 0.000 title description 2
- 239000002917 insecticide Substances 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 239000004480 active ingredient Substances 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 17
- 150000002923 oximes Chemical group 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 230000000749 insecticidal effect Effects 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 3
- 239000012876 carrier material Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000012764 mineral filler Substances 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- -1 oxyiminomethylcyclopropanecarboxylic acid esters Chemical class 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- 239000002253 acid Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 10
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- 239000000047 product Substances 0.000 description 9
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
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- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 6
- QDKIFIYGNKHERN-UHFFFAOYSA-N 4-(bromomethyl)-1-fluoro-2-phenoxybenzene Chemical compound FC1=CC=C(CBr)C=C1OC1=CC=CC=C1 QDKIFIYGNKHERN-UHFFFAOYSA-N 0.000 description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
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- 235000019341 magnesium sulphate Nutrition 0.000 description 4
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
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- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
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- 239000011780 sodium chloride Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
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- DRYYHCPKEDXXAR-UHFFFAOYSA-N 2,2-dimethyl-3-(2-methylpropoxyiminomethyl)cyclopropane-1-carboxylic acid Chemical compound CC(C)CON=CC1C(C(O)=O)C1(C)C DRYYHCPKEDXXAR-UHFFFAOYSA-N 0.000 description 2
- VSBPRBXTUAKKSY-UHFFFAOYSA-N 5-(5-methyl-1,3-dioxan-4-yl)-1,3-benzodioxole Chemical compound CC1COCOC1C1=CC=C(OCO2)C2=C1 VSBPRBXTUAKKSY-UHFFFAOYSA-N 0.000 description 2
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- 239000004033 plastic Substances 0.000 description 1
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- KYKNRZGSIGMXFH-ZVGUSBNCSA-M potassium bitartrate Chemical compound [K+].OC(=O)[C@H](O)[C@@H](O)C([O-])=O KYKNRZGSIGMXFH-ZVGUSBNCSA-M 0.000 description 1
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- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
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- 235000019354 vermiculite Nutrition 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
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Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33262181A | 1981-12-21 | 1981-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU191510B true HU191510B (en) | 1987-02-27 |
Family
ID=23299063
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU409782A HU191510B (en) | 1981-12-21 | 1982-12-20 | Insecticide and acaricide compositions containing fluoro-phenoxy-benzyl-esters and process for preparing the active substances |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS58116449A (cs) |
| CS (1) | CS241132B2 (cs) |
| HU (1) | HU191510B (cs) |
| PL (1) | PL132202B1 (cs) |
| ZA (1) | ZA829332B (cs) |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1410080A (en) * | 1972-12-21 | 1975-10-15 | Nat Res Dev | Oxime derivatives of 2,2-dimethyl-3-formyl cyclopropane carboxylic acid and their use as insecticides |
| US4282249A (en) * | 1978-06-02 | 1981-08-04 | Shell Oil Company | Oxyimino-substituted (1R, cis)-cyclopropanecarboxylate pesticides |
| DK158037C (da) * | 1978-06-02 | 1990-08-13 | Shell Int Research | Fremgangsmaade til bekaempelse af acari ved hjaelp af oxyimino-substituerede cyclopropancarboxylsyreestere og z-isomerer af visse af disse estere til brug ved fremgangsmaaden |
| US4254277A (en) * | 1978-06-02 | 1981-03-03 | Shell Oil Company | Oxyimino-substituted (1R, trans)-cyclopropanecarboxylic acids and derivatives thereof |
| US4211792A (en) * | 1978-06-02 | 1980-07-08 | Shell Oil Company | Oxyimino-substituted (1R,trans)-cyclopropanecarboxylate pesticides |
| US4292325A (en) * | 1979-02-21 | 1981-09-29 | Shell Oil Company | Oxyimino-substituted (1R,cis)cyclopropanecarboxylate pesticides |
| US4237123A (en) * | 1979-06-25 | 1980-12-02 | Shell Oil Company | Oxyimino-substituted cyclopropanecarboxylate pesticides |
| JPS5740440A (en) * | 1980-08-21 | 1982-03-06 | Yoshio Katsuta | New carboxylic ester derivative, its production, insecticide and acaricide containing the same |
| JPS5879909A (ja) * | 1981-11-07 | 1983-05-13 | Yoshio Katsuta | 低魚毒性殺虫・殺ダニ剤及びその製造法 |
-
1982
- 1982-12-20 ZA ZA829332A patent/ZA829332B/xx unknown
- 1982-12-20 HU HU409782A patent/HU191510B/hu not_active IP Right Cessation
- 1982-12-21 PL PL23965482A patent/PL132202B1/pl unknown
- 1982-12-21 JP JP57223121A patent/JPS58116449A/ja active Pending
- 1982-12-21 CS CS829470A patent/CS241132B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL132202B1 (en) | 1985-02-28 |
| CS947082A2 (en) | 1985-07-16 |
| ZA829332B (en) | 1983-09-28 |
| PL239654A1 (en) | 1983-08-29 |
| JPS58116449A (ja) | 1983-07-11 |
| CS241132B2 (en) | 1986-03-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |